3-Ethoxy-2-methylacrylaldehyde → (6-Methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol

HRID 859622Notes

Reaction equation

[NH2:1][C:2]1[NH:6][N:5]=[C:4]([CH2:7][OH:8])[N:3]=1.CCO/[CH:12]=[C:13](/[CH:15]=O)\[CH3:14]>C(O)(=O)C>[CH3:15][C:13]1[CH:12]=[N:1][C:2]2[N:6]([N:5]=[C:4]([CH2:7][OH:8])[N:3]=2)[CH:14]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a slurry of (5-amino-1H-[1,2,4]triazol-3-yl)-methanol (16.6 g, 87.6 mmol) from step 6 of example A(1) in acetic acid was added 3-ethoxymethacrolein (10 g, 87.6 mmol). The mixture was heated to 80° C. for 4 hours. Upon cooling of the reaction, the product cyrstallized out of solution. The collected product was awhite solid (14 g, 92%). 1H NMR (300 MHz, DMSO-d6): δ 2.38 (s, 3 H), 4.63 (s, 2 H), 5.52 (s, 1 H), 8.75 (s, 1 H), 9.21 (s, 1 H).

Workup

temperatureUpon cooling of the reaction

Sources & evidence

ORD record: ord-397600b6fbae4a279237d05e411ac914
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07151105B2

Reaction notes

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